Selective herbicide comprising a tetrazolinone derivative

ABSTRACT

The invention relates to novel herbicidal synergistic active compound combinations comprising a known tetrazolinone derivative and known herbicidally active compounds and/or safeners, which compositions can be used with particularly good results for the selective control of weeds in various crops of useful plants.

The invention relates to novel herbicidal synergistic active compoundcombinations comprising a known tetrazolinone derivative and knownherbicidally active compounds and/or safeners, which compositions can beused with particularly good results for the selective control of weedsin various crops of useful plants.

The tetrazolinone derivative4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide(common name: fentrazamide) is, as a broadly active herbicide, alone orin mixtures with other herbicides, the subject of a number of patentapplications (cf U.S. Pat. No. 5,362,704; JP 11335212A; JP2000239111 A;JP 10330202; JP 09241109 A; JP 09012406 A; U.S. Pat. No. 5,928,991; WO00/003,591; WO 00/003,597). However, the known herbicidal combinationshave a number of gaps in their activity, and their compatibility withcrop plants is likewise not under all conditions entirely satisfactory.

Surprisingly, it has now been found that the compound4-(2-chlorophenyl)-N-cyclo-hexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide,when used together with known herbicidally active compounds from variousclasses of substances, shows pronounced synergistic effects with respectto the activity against weeds and can be used particularlyadvantageously as broadly active combination preparations for theselective control of weeds in crops of useful plants such as, forexample, rice.

Surprisingly, it has also been found that the compound4-(2-chlorophenyl)-N-cyclo-hexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide,alone or together with known herbicidally active compounds, can, whenused together with the crop-plant-compatibility-improving compounds(safeners/antidotes) described below, prevent damage to the crop plantsextremely efficiently and can therefore be used in a particularlyadvantageous manner as a broadly active combination preparation for theselective control of weeds in crops of useful plants such as cereals,for example wheat, barley, rye and rice.

The present invention provides selective herbicidal compositions,comprising an effective amount of an active compound combinationcomprising

-   (a) the compound    4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide    (fentrazamide) of the general formula (I)-    and-   (b) one or more compounds from a second group of herbicides    comprising the active compounds listed below:    -   2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoic acid and its        salts, for example the sodium salt (bispyribac-sodium, known        from EP-A 321 846), diphenylmethanone        O-[2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoyl]-oxime        (pyribenzoxim, known from EP-A 658 549),        7-[(4,6-dimethoxy-2-pyrimidinyl)thio]-3-methyl-1        (3H)-isobenzofuranone (pyriftalid, known from WO 91/05781),        1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-(methyl-2-propynylamino)-1H-pyrazole-4-carbonitrile        (pyraclonil, known from WO 94/08999),        N-(2,6-dichloro-3-methylphenyl)-5,7-dimethoxy-[1,2,4]-triazolo[1,5-a]pyrimidine-2-sulphonamide        (metosulam),        2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulphonyl]-benzoic        acid (metsulfuron), methyl        3-chloro-5-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]-1-methyl-1H-pyrazole-4-carboxylate        (halosulfuron),        α-2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-4-fluorobenzenepropanoic        acid esters, in particular the ethyl ester        (carfentrazone-ethyl),        4-[2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulphonylbenzoyl]-5-hydroxy-1-methyl-1H-pyrazole        (known from WO 98/31681), 1-methylethyl        5-[4-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-2-chloro-4-fluorobenzoate        (fluazolate, known from WO 92/06962),        2-[1-[[2-(4-chlorophenoxy)propoxy]amino]-butyl]-5-(tetrahydro-2H-thiopyran-3-yl)-1,3-cyclohexanedione        (clefoxydim, known from EP 456112),        N-(2,4-difluorophenyl-1,5-dihydro-N-1-propyl-5-oxo-1-[(tetrahydro-2H-pyran-2-yl)methyl]-4H-1,2,4-triazole-4-carboxamide        (HOK-201-cf. WO-A-98/38176/U.S. Pat. No. 6,077,814),        4-(7-chloro-2,4-dimethyl-5-benzofuranyl)-2,4-dihydro-2-methyl-5-trifluoromethyl-3H-1,2,4-triazol-3-thione        (OK-701-cf. WO-A-97/09326/U.S. Pat. No. 5,759,958),        [2-chloro-3-(4,5-dihydro-3-isoxazolyl)-4-methylsulphonylphenyl]-(5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone        (cf. WO-A-96/26206, WO-A-98/31681),        [3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-methylsulphonylphenyl]-(5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone        (cf. WO-A-96/26206, WO-A-98/31681),        [3-[2-chloro-3-[(2,6-dioxocyclohexyl)carbonyl]-6-ethylsulphonylphenyl]-5-isoxazolyl]acetonitrile        (cf. WO-A-01/28341),        2-[2-chloro-4-methyl-sulphonyl-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-1,3-cyclohexanedione        (cf. WO-A-01/28341) and        2-[[5,8-dimethyl-1,1-dioxido-4-(2-pyrimidinyl-oxy)-3,4-dihydro-2H-thiochromen-6-yl]-carbonyl]-1,3-cyclohexanedione        (cf. WO-A-01/28341);    -   (“active compound of group 2”),    -   and, if appropriate,-   (c) at least one compound which improves crop plant compatibility,    from the following group of compounds:    -   α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile        (oxabetrinil), α-(cyano-methoximino)phenylacetonitrile        (cyometrinil),        4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone        oxime (fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim),        4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine        (benoxacor), 1-methylhexyl 5-chloroquinoxaline-8-oxyacetate        (cloquintocet), 2,2-dichloro-N-(2-oxo-2-(2-propenyl        amino)ethyl)-N-(2-propenyl)acetamide (DKA-24), 1,8-naphthalic        anhydride, ethyl        1-(2,4-di-chlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate        (fenchlorazole ethyl), phenylmethyl        2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),        3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine        (furilazole, MON-13900),        4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67),        2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),        2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide        (PPG-1292), 2,2-dichloro-N,N-di-2-propenylacetamide        (dichlormid), N-(4-methylphenyl)-N′-(1-methyl-1-phenylethyl)urea        (dymron),        1-dichloroacetylhexahydro-3,3,8a-trimethyl-pyrrolo[1,2-a]pyrimidin-6(2H)one        (BAS-145138),        N-(2-methoxybenzoyl)-4-(methylaminocarbonylamino)benzenesulphonamide,        ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate        (isoxadifen-ethyl), (4-chloro-2-methylphenoxy)acetic acid        (MCPA), 2-(4-chloro-2-methylphenoxy)propionic acid (meco-prop),        diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazol-3,5-dicarboxylate        (mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D)        and its derivatives,        4-(2-chlorobenzoylaminosulphonyl)-N-propylbenzamide and other        N-(phenylsulphamoyl)benzanmide derivatives of the formula (II)    -   in which    -   R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,        (C₂-C₆)-alkenyl, (C₅-C₆)-cycloalkenyl, phenyl or 3- to        6-membered heterocyclyl having up to 3 hetero atoms from the        group consisting of nitrogen, oxygen and sulphur, where the six        last-mentioned radicals are optionally substituted by one or        more identical or different substituents from the group        consisting of halogen, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,        (C₁-C₂)-alkylsulphinyl, (C₁-C₂)-alkylsulphonyl,        (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxycarbonyl,        (C₁-C₄)-alkylcarbonyl and phenyl and, in the case of cyclic        radicals, also (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl;    -   R² represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,        (C₂-C₆)-alkynyl, where the three last-mentioned radicals are        optionally substituted by one or more identical or different        substituents from the group consisting of halogen, hydroxyl,        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-alkylthio;    -   R³ represents halogen, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,        nitro, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylsulphonyl,        (C₁-C₄)— alkoxycarbonyl or (C₁-C₄)-alkylcarbonyl;    -   R⁴ represents hydrogen or methyl;    -   R⁵ represents halogen, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-haloalkoxy, (C₃-C₆)-cycloalkyl, phenyl, (C₁-C₄)-alkoxy,        cyano, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl,        (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-alkoxycarbonyl or        (C₁-C₄)-alkylcarbonyl;    -   n represents 0, 1 or 2 and    -   m represents 1 or 2,    -   and their salts, in particular the sodium salts (known from        WO-099/16744) or        2-methoxy-N-[4-(2-methoxybenzoylsulphamoyl)phenyl]acetamide and        other N-acylsulphonamide derivatives of the formula (III)    -   in which    -   R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,        furanyl or thienyl, where each of the four last-mentioned        radicals is unsubstituted or substituted by one or more        substituents from the group consisting of halogen,        (C₁-C₄)-alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₄)-alkylthio and,        in the case of cyclic radicals, also (C₁-C₄)-alkyl and        (C₁-C₄)-haloalkyl;    -   R² represents hydrogen or methyl;    -   R³ represents halogen, halo-(C₁-C₄)-alkyl, halo-(C₁-C₄)-alkoxy,        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylsulphonyl,        (C₁-C₄)-alkoxy-carbonyl or (C₁-C₄)-alkylcarbonyl;    -   R⁴ represents hydrogen or methyl;    -   R⁵ represents halogen, (C₁-C₄)-alkyl, halo-(C₁-C₄)-alkyl,        halo-(C₁-C₄)-alkoxy, (C₃-C₆)-cycloalkyl, phenyl, (C₁-C₄)-alkoxy,        cyano, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl,        (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-alkoxycarbonyl or        (C₁-C₄)-alkylcarbonyl;    -   n represents 0, 1 or 2 and    -   m represents 1 or 2,    -   and their alkali metal salts, in particular the sodium salts        (known from DE-Al-19 621 522)    -   (“active compounds of group 3”).

As components for mixtures preference is given to the following activecompounds of group 2:

-   bispyribac-sodium and pyribenzoxim.

Surprisingly, it has now been found that the active compoundcombinations defined above of the tetrazolinone derivative of theformula (I) and the active compounds of group 2 listed above incombination with active compounds of group 3, whilst being very welltolerated by useful plants, have particularly high herbicidal activityand can be used in a variety of crops, in particular in rice, but alsoin maize and cereals, for the selective control of weeds.

Surprisingly, the herbicidal activity of the active compoundcombinations according to the invention of compounds of theabovementioned groups 1 and 2 is considerably higher than the sum of theactivities of the individual active compounds.

This means that there is not only a complementary action but also anunforeseeable synergistic effect. The novel active compound combinationsare tolerated well by a large number of crops, and the novel activecompound combinations also effectively control weeds which are otherwisedifficult to control. The novel active compound combinations aretherefore a valuable addition to the selective herbicides of the priorart.

Moreover, surprisingly, it has been found that the active compoundcombinations defined above of the tetrazolinone derivative of theformula (I) and a safener/antidote (“active compounds of group 3”) incombination with one or more of the active compounds of group 2 listedabove, in addition to being very well tolerated by useful plants, haveparticularly high herbicidal activity and can be used in a variety ofcrops, in particular in cereal, especially wheat, but also in soybeans,potatoes, maize and rice, for the selective control of weeds.

It is furthermore surprising that, from a large number of known safenersor antidotes capable of antagonizing the damaging effect of a herbicideon the crop plants, it is specifically the compounds of group (c) listedabove which neutralize the damaging effect of compounds of the formula(I) and their salts, if appropriate in combination with one or more ofthe active compounds of group 2 listed above, on the crop plantsvirtually completely without adversely affecting the herbicidal activityagainst the weeds.

It may be mentioned that the compositions according to the invention canbe modified such that, in addition to components (a) and (b), theycomprise, as third or further herbicidally active compound, one or moreof the following active compounds:

2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide(acetochlor), 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acidsodium salt (acifluorfen-sodium), 2-chloro-6-nitro-3-phenoxybenzeneamine(aclonifen), 2-chloro-N-(meth-oxymethyl)-N-(2,6-diethylphenyl)acetamide(alachlor), N-ethyl-N′-1-propyl-6-methylthio-1,3,5-triazine-2,4-diamine(ametryn),4-amino-N-(1,1-dimethylethyl)-4,5-dihydro-3-(1-methylethyl)-5-oxo-1H-1,2,4-triazole-1-carboxamide(amicarbazone),N-(4,6-dimethoxy-pyrimidin-2-yl)-N′-(N-methyl-N-methylsulphonylsulphamoyl)urea(amidosulfuron), 1H-1,2,4-triazol-3-amine (amitrole),S-[2-[(4-chlorophenyl)-(1-isopropyl)amino]-2-oxoethyl]O,O-dimethylphosphorodithioate (anilofos),6-chloro-4-ethylamino-2-isopropylamino-1,3,5-triazine (atrazine),2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]-pyridin-3(2H)-one(azafenidin),N-(4,6-dimethoxypyrimidin-2-yl)-N′-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazol-5-ylsulphonyl]urea(azimsulfuron), N-benzyl-2-(4-fluoro-3-trifluoromethylphenoxy)butanamide(beflubutamid), 4-chloro-2-oxo-3(2H)-benzothiazoleacetic acid(benazolin), N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethyl-benzene-amine(benfluralin), 2,3-dihydro-3,3-dimethyl-5-benzofuranylethanesulphonate(benfuresate),N-(4,6-dimethoxypyrimidin-2-yl)-N′-(2-methoxycarbonylphenylmethyl-sulphonyl)urea(bensulfuron-methyl), S-[(4-chlorophenyl)methyl]diethylthiocarbamate(benthiocarb, thiobencarb), methyl2-[2-[4-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinylphenoxymethyl]-5-ethylphenoxypropanoate (benzfendizone),3-(2-chloro-4-methylsulphonylbenzoyl)-4-phenylthio-bicyclo-[3.2.1]-oct-3-en-2-one(benzobicyclon),2-[[4-(2,4-dichloro-3-methyl-benzoyl)-1,3-dimethyl-1H-pyrazol-5-yl]-oxy]-1-(4-methylphenyl)ethanone(benzofenap), ethyl N-benzoyl-N-(3,4-dichlorophenyl)-DL-alaninate(benzoylprop-ethyl), 3-1-propyl-1H-2,1,3-benzothiadiazin-4(3H)-one(bentazone), methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate (bifenox),5-bromo-6-methyl-3-(1-methylpropyl)-2,4(1H,3H)pyrimidinedione(bromacil), 2-bromo-3,3-dimethyl-N-(1-methyl-1-phenylethyl)butanamide(bromobutide), 3,5-dibromo-4-hydroxy-benzaldehyde0-(2,4-dinitrophenyl)-oxime (bromofenoxim),3,5-dibromo-4-hydroxybenzonitrile (bromoxynil),N-butoxymethyl-2-chloro-N-(2,6-diethylphenyl)acetamide (butachlor),[1,1-dimethyl-2-oxo-2-(2-propenyloxy)]ethyl2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl)benzoate (butafenacil-allyl),2-(1-ethoximinopropyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(1-oxobutyl)phenyl]-2-cyclohexen-1-one(butroxydim), S-ethyl bis-(2-methylpropyl)thiocarbamate (butylate),N,N-diethyl-3-(2,4,6-trimethylphenylsulphonyl)-1H-1,2,4-triazole-1-carboxamide(cafenstrole),2-[1-[(3-chloro-2-propenyl)oxyimino]propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen-1-one(caloxydim, tepraloxydim),2-(4-chloro-2-fluoro-5-(2-chloro-2-ethoxycarbonylethyl)phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one(carfentrazone-ethyl),2,4-dichloro-1-(3-methoxy-4-nitro-phenoxy)-benzene (chlomethoxyfen),3-amino-2,5-dichlorobenzoic acid (chloramben),N-(4-chloro-6-methoxypyrimidin-2-yl)-N′-(2-ethoxycarbonylphenylsulphonyl)-urea(chlorimuron-ethyl), 1,3,5-trichloro-2-(4-nitrophenoxy)benzene(chlornitrofen),N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(2-chlorophenylsulphonyl)urea(chlorsulfuron), N′-(3-chloro-4-methylphenyl)-N,N-dimethylurea(chlortoluron), ethyl2-chloro-3-[2-chloro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propanoate(cinidon-ethyl),exo-1-methyl-4-isopropyl-2-(2-methylphenylmethoxy)-7-oxabicyclo-[2.2.1]-heptane(cinmethylin),N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N′-(2-(2-methoxyethoxy)phenylsulphonyl)urea(cinosulfuron),2-[1-[2-(4-chloro-phenoxy)propoxyaminobutyl]-5-(tetrahydro-2H-thiopyran-3-yl)-1,3-cyclohexanedione(clefoxydim),(E,E)-(+)-2-[1-[[(3-chloro-2-propenyl)oxy]imino]propyl]-3-hydroxy-2-cyclohexen-1-one(clethodim), (R)-(2-propynyl)2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxypropanoate(clodinafop-propargyl),2-(2,4-dichloro-3-methylphenoxy)-N-phenylpropanamide (clomeprop),3,6-dichloropyridine-2-carboxylic acid (clopyralid), methyl3-chloro-2-[(5-ethoxy-7-fluoro[1,2,4]triazolo-[1,5-c]pyrimidin-2-ylsulphonyl)amino]benzoate(cloransulam-methyl),N-[(2-chlorophenyl)methyl]-N′-(1-methyl-1-phenylethyl)urea (cumyluron),2-chloro-4-ethylamino-6-(1-cyano-1-methylethylamino)-1,3,5-triazine(cyanazine),N-(4,6-dimethoxypyrimidin-2-yl)-N′-(2-cyclopropylcarbonylphenylsulphonyl)urea(cyclosulfamuron),2-(1-ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-1-one(cycloxydim), (R)-2-butyl[4-(4-cyano-2-fluorophenoxy)phenoxy]-propanoate (cyhalofop-butyl),2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxybenzoicacid (dicamba), (R)-2-(2,4-dichlorophenoxy)propanoic acid(dichlorprop-P), methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate(diclofop-methyl),N-(2,6-dichlorophenyl)-5-ethoxy-7-fluoro-[1,2,4]-triazolo-[1,5-c]-pyrimidine-2-sulphonamide(diclosulam), 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methylsulphate(difenzoquat),N-(2,4-difluorophenyl)-2-(3-trifluoromethylphenoxy)pyridine-3-carboxamide(diflufenican),2-[1-[(3,5-difluorophenyl)-aminocarbonyl-hydrazono]ethyl]pyridine-3-carboxylicacid (diflufenzopyr), S-(1-methyl-1-phenylethyl)-1-piperidinecarbothioate (dimepiperate),2-chloro-N-(2,6-dimethyl-phenyl)-N-(2-methoxyethyl)acetamide(dimethachlor),N-(1,2-dimethylpropyl)-N′-ethyl-6-methylthio-1,3,5-triazine-2,4-diamine(dimethametryn), (S-)2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide((S-) (dimethenamid)),2-amino-4-(1-fluoro-1-methylethyl)-6-(1-methyl-2-(3,5-dimethylphenoxy)ethyl-amino)-1,3,5-triazine(dimexyflam),N3,N3-diethyl-2,4-dinitro-6-trifluoromethyl-1,3-diaminobenzene(dinitramine), 6,7-dihydrodipyrido[1,2-a:2′,1′-c]pyrazinediium (diquat),S,S-dimethyl2-difluoromethyl-4-1-butyl-6-trifluoromethylpyridine-3,5-dicarbothioate(dithiopyr), N′-(3,4-dichlorophenyl)-N,N-dimethylurea (diuron),N-(4-methylphenyl)-N′-(1-methyl-1-phenylethyl)urea (dymron, daimuron),2-[2-(3-chlorophenyl)oxiranylmethyl]-2-ethyl-1H-indene-1,3(2H)-dione(epropodan), S-ethyl dipropylthiocarbamate (EPTC),S-(phenylmethyl)-N-ethyl-N-(1,2-dimethylpropyl)thiocarbamate(esprocarb),N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-trifluoromethylbenzeneamine(ethalfluralin), (S)-(2-ethoxy-1-methyl-2-oxoethyl)2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoate (ethoxyfen),N-(4,6-dimethoxypyrimidin-2-yl)-N′-(2-ethoxyphenoxysulphonyl)urea(ethoxysulfuron), N-(2,3-dichlorophenyl)-4-ethoxymethoxybenzamide(etobenzanid), (R)-ethyl2-[4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propanoate(fenoxaprop-(P)-ethyl), isopropylN-benzoyl-N-(3-chloro-4-fluorophenyl)-DL-alaninate (flamprop-isopropyl),isopropyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-L-alaninate(flamprop-isopropyl-L), methylN-benzoyl-N-(3-chloro-4-fluorophenoxy)-DL-alaninate (flamprop-methyl),N-(2,6-difluorophenyl)-8-fluoro-5-methoxy-[1,2,4]-triazolo-[1,5-c]-pyrimidine-2-sulphonamide(florasulam), (R)-butyl2-[4-(5-trifluoromethylpyridin-2-yloxy)phenoxy]-propanoate (fluazifop,-butyl, -P-butyl), i-propyl5-(4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-2-chloro-4-fluorobenzoate(fluazolate),4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[(2-trifluoromethoxyphenyl)sulphonyl]-1-H-1,2,4-triazole-1-carboxamidesodium salt (flucarbazone-sodium),N-(4-fluorophenyl)-N-1-propyl-2-(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)acetamide(flufenacet),N-(2,6-difluorophenyl)-5-methyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulphonamide(flumetsulam), pentyl[2-chloro-4-fluoro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]acetate(flumiclorac-pentyl),2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]4,5,6,7-tetrahydro-1H-isoindole-1,3-ione(flumioxazin),2-[4-chloro-2-fluoro-5-[(1-methyl-2-propynyl)oxy]phenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione(flumipropyn),3-chloro-4-chloromethyl-1-(3-trifluoromethylphenyl)-2-pyrrolidinone(fluorochloridone), ethoxycarbonylmethyl5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate(fluoroglycofen-ethyl),1-(4-chloro-3-(2,2,3,3,3-pentafluoropropoxymethyl)phenyl)-5-phenyl-1H-1,2,4-triazol-3-carboxamide(flupoxam),1-isopropyl-2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidyl)benzoate (flupropacil),N-(4,6-dimethoxypyrimidin-2-yl)-N′-(3-methoxycarbonyl-6-trifluoromethylpyridin-2-ylsulphonyl)ureasodium salt (flupyrsulfuron-methyl-sodium),9-hydroxy-9H-fluorene-9-carboxylic acid (flurenol),(4-amino-3,5-dichloro-6-fluoropyridin-2-yloxy)acetic acid(2-butoxy-1-methyl-ethyl ester, 1-methyl-heptyl ester) (fluroxypyr,-butoxypropyl, -meptyl),5-methylamino-2-phenyl-4-(3-trifluoromethylphenyl)-3(2H)-furanone(flurtamone), methyl[(2-chloro-4-fluoro-5-(tetrahydro-3-oxo-1H,3H-[1,3,4]-thiadiazolo-[3,4-a]-pyridazin-1-ylidene)aminophenyl]thioacetate(fluthiacet-methyl),5-(2-chloro-4-trifluoromethylphenoxy)-N-methylsulphonyl-2-nitrobenzamide(fomesafen),2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]-4-formylamino-N,N-dimethylbenzamide(foramsulfuron), 2-amino-4-(hydroxymethylphosphinyl)butanoic acid(ammonium salt) (glufosinate (ammonium)), N-phosphonomethylglycine(isopropylammonium salt), (glyphosate, isopropylammonium),(R)-2-[4-(3-chloro-5-trifluoromethylpyridin-2-yl-oxy)phenoxy]propanoicacid (methyl ester, 2-ethoxyethyl ester, butyl ester) (haloxyfop,-methyl, -P-methyl, -ethoxyethyl, -butyl),3-cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione(hexazinone), methyl2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-4-methylbenzoate(imazamethabenz-methyl),2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-methylpyridine-3-carboxylicacid (imazamethapyr),2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-5-methoxymethylpyridine-3-carboxylicacid (imazamox),2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-quinoline-3-carboxylicacid (imazaquin),2-(4,5-dihydro-4-methyl-4-1-propyl-5-oxo-1H-imidazol-2-yl)-5-ethylpyridine-3-carboxylicacid (imazethapyr),N-(4,6-dimethoxypyrimidin-2-yl)-N′-(2-chloro-imidazo[1,2-a]-pyridin-3-ylsulphonyl)urea(imazosulfuron),N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(5-iodo-2-methoxycarbonylphenylsulphonyl)ureasodium salt (iodosulfuron-methyl-sodium),4-hydroxy-3,5-diiodobenzonitrile (ioxynil),N,N-dimethyl-N′-(4-isopropylphenyl)urea (isoproturon),N-(3-(1-ethyl-1-methylpropyl)-isoxazol-5-yl)-2,6-dimethoxybenzamide(isoxaben),(4-chloro-2-methylsulphonyl-phenyl)-(5-cyclopropylisoxazol-4-yl)methanone(isoxachlortole),(5-cyclopropylisoxazol-4-yl)(2-methylsulphonyl-4-trifluoromethylphenyl)methanone(isoxaflutole),2-[2-[4-[3,5-dichloro-2-pyridinyl)oxy]phenoxy]-1-oxo-propyl]isoxazolidine(isoxapyrifop), (2-ethoxy-1-methyl-2-oxoethyl)5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate (lactofen),N′-(3,4-dichlorophenyl)-N-methoxy-N-methylurea (linuron),(4-chloro-2-methylphenoxy)acetic acid (MCPA),2-(4-chloro-2-methylphenoxy)propionic acid (mecoprop),2-(2-benzothiazolyloxy)-N-methyl-N-phenylacetamide (mefenacet), methyl2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]-4-[[(methylsulphonyl)amino]methyl]benzoate(mesosulfuron),2-(4-methylsulphonyl-2-nitrobenzoyl)-1,3-cyclohexanedione (mesotrione),4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (metamitron),2-chloro-N-(2,6-dimethylphenyl)-N-(1H-pyrazol-1-ylmethyl)acetamide(metazachlor),N′-(4-(3,4-dihydro-2-methoxy-2,4,4-trimethyl-2H-1-benzopyran-7-yl-oxy)phenyl)-N-methoxy-N-methylurea(metobenzuron), N′-(4-bromophenyl)-N-methoxy-N-methylurea(metobromuron),(S)-2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide(metolachlor, S-metolachlor),N-(2,6-dichloro-3-methylphenyl)-5,7-dimethoxy-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulphonamide(metosulam), N′-(3-chloro-4-methoxyphenyl)-N,N-dimethylurea (metoxuron),4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)one (metribuzin),N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(2-methoxycarbonylphenylsulphonyl)urea(metsulfuron-methyl), S-ethyl hexahydro-1H-azepin-1-carbothioate(molinate), 2-(2-naphthyloxy)-N-phenylpropanamide (naproanilide),N-butyl-N′-(3,4-dichlorophenyl)-N-methylurea (neburon),N-(4,6-dimethoxypyrimidin-2-yl)-N′-(3-dimethylcarbamoylpyridin-2-yl-sulphonyl)urea(nicosulfuron),4-chloro-5-methylamino-2-(3-trifluoromethylphenyl)-3(2H)pyridazinone(norflurazon), S-(2-chlorobenzyl) N,N-diethylthiocarbamate (orbencarb),4-dipropylamino-3,5-dinitrobenzenesulphonamide (oryzalin),3-[2,4-dichloro-5-(2-propynyloxy)phenyl]-5-(t-butyl)-1,3,4-oxadiazol-2(3H)one(oxadiargyl),3-[2,4-dichloro-5-(1-methylethoxy)-phenyl]-5-(t-butyl)-1,3,4-oxadiazol-2(3H)one(oxadiazon),N-(4,6-dimethylpyrimidin-2-yl)-N′-(2-oxetan-3-yloxycarbonylphenylsulphonyl)urea(oxasulfuron),3-[1-(3,5-dichlorophenyl)-1-1-propyl]-2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazin-4-one(oxaziclomefone),2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-trifluoromethylbenzene(oxyfluorfen), 1,1′-dimethyl-4,4′-bipyridinium (paraquat),1-amino-N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzene(pendimethalin), 4-(t-butyl)-N-(1-ethylpropyl)-2,6-dinitrobenzeneamine(pendralin),3-(4-chloro-5-cyclopentyloxy-2-fluorophenyl)-5-(1-methylethylidene)-2,4-oxazolidinedione(pentoxazone), 4-amino-3,5,6-trichloropyridine-2-carboxylic acid(picloram),N-(4-fluorophenyl)-6-(3-trifluoromethylphenoxy)pyridine-2-carboxamide(picolinafen), S-[2-(2-methyl-1-piperidinyl)-2-oxoethyl]O,O-dipropylphosphorodithioate (piperophos),2-chloro-N-(2,6-diethylphenyl)-N-(2-propoxyethyl)acetamide(pretilachlor),N-(4,6-bis-difluoromethoxypyrimidin-2-yl)-N′-(2-methoxycarbonyl-phenylsulphonyl)urea(primisulfuron-methyl),1-chloro-N-[2-chloro-4-fluoro-5-[(6S,7aR)-6-fluorotetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl]phenyl]methanesulphonamide(profluazol), 2-chloro-N-isopropyl-N-phenylacetamide (propachlor),N-(3,4-dichlorophenyl)propanamide (propanil),(R)-[2-[[(1-methylethylidene)amino]oxy]ethyl]2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propanoate(propaquizafop),2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(1-methylethoxy)methyl]acetamide(propisochlor), methyl2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]-sulphonyl]benzoatesodium salt (propoxycarbazone-sodium),S-phenylmethyl-N,N-dipropylthiocarbamate (prosulfocarb),N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(2-(3,3,3-trifluoropropyl)phenylsulphonyl)urea(prosulfuron), ethyl[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorophenoxy]acetate(pyraflufen-ethyl),1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-(methyl-2-propynylamino)-1H-pyrazole-4-carbonitrile(pyraclonil, pyrazogyl),4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-(4-methylphenylsulphonyloxy)pyrazole(pyrazolate),4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-(phenylcarbonylmethoxy)pyrazole(pyrazoxyfen),N-(4,6-dimethoxypyrimidin-2-yl)-N′-(4-ethoxycarbonyl-1-methylpyrazol-5-ylsulphonyl)urea(pyrazosulfuron-ethyl), diphenylmethanoneO-[2,6-bis-(4,6-dimethoxypyrimidin-2-yloxy)benzoyl]oxime (pyribenzoxim),O-[3-(1,1-dimethyl-ethyl)phenyl](6-methoxy-2-pyridinyl)methylthiocarbamate(pyributicarb), 6-chloro-3-phenyl-4-pyridazinol (pyridafol),O-(6-chloro-3-phenylpyridazin-4-yl) S-octyl thiocarbonate (pyridate),6-chloro-3-phenylpyridazin-4-ol (pyridatol),7-[(4,6-dimethoxy-2-pyrimidinyl)thio]-3-methyl-[(3H)-isobenzofuranone(pyriftalid), methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)benzoate(pyriminobac-methyl),2-chloro-6-(4,6-dimethoxypyrimidin-2-ylthio)benzoic acid sodium salt(pyrithiobac-sodium), 3,7-dichloroquinoline-8-carboxylic acid(quinchlorac), 7-chloro-3-methylquinoline-8-carboxylic acid (quinmerac),2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propanoic acid (ethyl ester,tetrahydro-2-furanylmethyl ester) (quizalofop, -ethyl, -P-ethyl,-P-tefuryl),N-(4,6-dimethoxypyrimidin-2-yl)-N′-(3-ethylsulphonylpyridin-2-ylsulphonyl)urea(rimsulfuron),2-(1-ethoximinobutyl)-5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohexen-1-one(sethoxydim), 6-chloro-2,4-bisethylamino-1,3,5-triazine (simazine),2-(2-chloro-4-methylsulphonylbenzoyl)-cyclohexane-1,3-dione(sulcotrione),2-(2,4-dichloro-5-methylsulphonylaminophenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one(sulfentrazone), methyl2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]benzoate(sulfometuron-methyl), N-phosphonomethylglycinetrimethylsulphonium(sulfosate),N-(4,6-dimethoxypyrimidin-2-yl)-N′-(2-ethylsulphonylimidazo[1,2-a]pyridine-3-sulphonamide(sulfosulfuron), 6-chloro-4-ethylamino-2-tert-butylamino-1,3,5-triazine(terbuthylazine),2-tert-butylamino-4-ethylamino-6-methylthio-1,3,5-triazine (terbutryn),2-chloro-N-(2,6-dimethylphenyl)-N-(3-methoxy-2-thienylmethyl)acetamide(thenylchlor), methyl2-difluoromethyl-5-(4,5-dihydrothiazol-2-yl)-4-(2-methylpropyl)-6-trifluoromethylpyridine-3-carboxylate(thiazopyr),6-(6,7-dihydro-6,6-dimethyl-3H,5H-pyrrolo[2,1-c]-1,2,4-thiadiazol-3-ylideneamino)-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one(thidiazimin),N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(2-methoxycarbonyl-thien-3-ylsulphonyl)urea(thifensulfuron-methyl),2-(ethoximinopropyl)-3-hydroxy-5-(2,4,6-trimethylphenyl)-2-cyclohexen-1-one(tralkoxydim), S-(2,3,3-trichloro-2-propenyl) diisopropylcarbamothioate(triallate),N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-[2-(2-chloroethoxy)phenylsulphonyl]urea(triasulfuron),N-methyl-N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(2-methoxycarbonylphenylsulphonyl)urea(tribenuron-methyl), (3,5,6-trichloro)pyridin-2-yloxyacetic acid-(triclopyr), 2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane(tridiphane),N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(2,2,2-trifluoroethoxy)-2-pyridinesulphonamidesodium salt (trifloxysulfuron),1-amino-2,6-dinitro-N,N-dipropyl-4-trifluoromethylbenzene (trifluralin),N-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]-N′-(2-methoxycarbonylphenylsulphonyl)urea(triflusulfuron-methyl),N-(4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2-yl)-N′-(2-trifluoromethylphenylsulphonyl)urea(tritosulfuron),N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(N-methyl-N-methylsulphonylamino])-2-pyridine-sulphonamide,(cf WO-92/10660),4-[4,5-dihydro-4-methyl-5-oxo-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl]-2-(ethylsulphonylamino)-5-fluorobenzenecarbothioamide(cf. WO-95/30661), phenylcarbothiamide,4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-2-[(ethylsulphonyl)amino]-5-fluoro—(CASNo. 173980-17-1, HWH4991) and2-chloro-N-[1-(2,6-dichloro-4-difluoromethylphenyl)-4-nitro-1H-pyrazol-5-yl]propanecarboxamide(CAS No. 121750-17-2; SLA5599).

Also preferably suitable for use as third or further active compoundsare: acetochlor acetochlor + dichlormid acetochlor + furilazoleacetochlor + R-29148 alachlor amicarbazone amidosulfuron anilofosanilofos + 2,4-D anilofos + propanil anilofos + quinoclamine atrazineazimsulfuron azimsulfuron + dymron azimsulfuron + anilofosazimsulfuron + benfuresate azimsulfuron + bensulfuron azimsulfuron +butachlor azimsulfuron + cafenstrole azimsulfuron + cyhalofop-butylazimsulfuron + dimepiperate azimsulfuron + esprocarb azimsulfuron +mefenacet azimsulfuron + indanofan azimsulfuron + oxaziclomefoneazimsulfuron + pretilachlor azimsulfuron + thenylchlor azimsulfuron +anilofos + dymron azimsulfuron + benfuresate + dymron azimsulfuron +bensulfuron + cafenstrole azimsulfuron + bensulfuron + cyhalofop-butylazimsulfuron + bensulfuron + dymron azimsulfuron + bensulfuron +dimethametryn azimsulfuron + bensulfuron + indanofan azimsulfuron +bensulfuron + pretilachlor azimsulfuron + bensulfuron + thenylchlorazimsulfuron + butachlor + dymron azimsulfuron + cafenstrole + dymronazimsulfuron + cyhalofop-butyl + dymron azimsulfuron + mefenacet +dymron azimsulfuron + oxaziclomefone + dymron azimsulfuron +pretilachlor + dymron benfuresate bensulfuron-methylbensulfuron-methyl + dymron bensulfuron-methyl + anilofosbensulfuron-methyl + benfuresate bensulfuron-methyl + butachlorbensulfuron-methyl + cafenstrole bensulfuron-methyl + cyhalofop-butylbensulfuron-methyl + dimepiperate bensulfuron-methyl + dithiopyrbensulfuron-methyl + esprocarb bensulfuron-methyl + indanofanbensulfuron-methyl + mefenacet bensulfuron-methyl + metsulfuron-methylbensulfuron-methyl + molinate bensulfuron-methyl + oxaziclomefonebensulfuron-methyl + pretilachlor bensulfuron-methyl + pyributicarbbensulfuron-methyl + quinclorac bensulfuron-methyl + thenylchlorbensulfuron-methyl + anilofos + dymron bensulfuron-methyl +benfuresate + dymron bensulfuron-methyl + butachlor + dymronbensulfuron-methyl + benfuresate + dimepiperate bensulfuron-methyl +benfuresate + pretilachlor bensulfuron-methyl + cafenstrole + dymronbensulfuron-methyl + cafenstrole + cyhalofop-butyl bensulfuron-methyl +cyhalofop-butyl + dymron bensulfuron-methyl + cyhalofop-butyl +thenylchlor bensulfuron-methyl + dithiopyr + quincloracbensulfuron-methyl + mefenacet + dymron bensulfuron-methyl + mefenacet +benthiocarb bensulfuron-methyl + mefenacet + molinatebensulfuron-methyl + oxaziclomefone + dymron bensulfuron-methyl +pretilachlor + dymron bensulfuron-methyl + pyributicarb + dymronbentazone bentazone + quinclorac benthiocarb (thiobencarb) benthiocarb +chlornitrofen benthiocarb + propanil benthiocarb + simetrynbenzobicyclon benzofenap benzofenap + thenylchlor + cumyluron bifenoxbifenox + pretilachlor bifenox + thenylchlor bispyribac-sodiumbispyribac-sodium + benthiocarb bromobutide bromobutide + pyrazoxyfenbromobutide + benzofenap + pyributicarb bromobutide + bifenox +pyrazolate bromobutide + pyrazoxyfen + thenylchlor butachlor butachlor +chlomethoxyfen butachlor + oxadiazon butachlor + propanil butachlor +pyrazolate butamifos butamifos + bromobutide butenachlor cafenstrolecafenstrole + dymron cafenstrole + cyhalofop-butyl + dymroncarfentrazone-ethyl chlomethoxyfen chlornitrofen chlornitrofen + dymroncinmethylin cinmethylin + 2,4-D cinosulfuron cinosulfuron + dymroncinosulfuron + anilofos cinosulfuron + benfuresate cinosulfuron +butachlor cinosulfuron + cafenstrole + dymron cinosulfuron +cyhalofop-butyl cinosulfuron + dimepiperate cinosulfuron + esprocarbcinosulfuron + mefenacet cinosulfuron + mefenacet + dymroncinosulfuron + molinate cinosulfuron + oxaziclomefone cinosulfuron +pretilachlor cinosulfuron + pretilachlor + dymron cinosulfuron +pretilachlor + fenclorim cinosulfuron + pretilachlor + quincloraccinosulfuron + pyriftalid clefoxydim clodinafop-propargylclodinafop-propargyl + cloquintocet-mexyl clomazone clomazone + propanilclomeprop clomeprop + pretilachlor cumyluron cyanazine cyclosulfamuroncyclosulfamuron + dymron cyclosulfamuron + anilofos cyclosulfamuron +benfuresate cyclosulfamuron + butachlor cyclosulfamuron + cafenstrole +dymron cyclosulfamuron + cyhalofop-butyl cyclosulfamuron + dimepiperatecyclosulfamuron + esprocarb cyclosulfamuron + mefenacetcyclosulfamuron + mefenacet + dymron cyclosulfamuron + oxaziclomefonecyclosulfamuron + pentoxazone cyclosulfamuron + pretilachlorcyclosulfamuron + quinclorac cyhalofop-butyl cyhalofop-butyl + bentazon2,4-D dichlorprop-P diethatyl-ethyl dimepiperate dimethametryndimethametryn + piperophos dimethenamid S-dimethenamid dithiopyr dymronesprocarb ethoxysulfuron ethoxysulfuron + dymron ethoxysulfuron +anilofos ethoxysulfuron + anilofos + dymron ethoxysulfuron + benfuresateethoxysulfuron + anilofos + benfuresate ethoxysulfuron + benfuresate +dymron ethoxysulfuron + butachlor ethoxysulfuron + cafenstroleethoxysulfuron + cafenstrole + dymron ethoxysulfuron + cyhalofop-butylethoxysulfuron + dimepiperate ethoxysulfuron + esprocarbethoxysulfuron + mefenacet ethoxysulfuron + mefenacet + dymronethoxysulfuron + oxaziclomefone ethoxysulfuron + pretilachlor + dymronethoxysulfuron + pretilachlor + pyrazolate etobenzanidfenoxaprop-(P)-ethyl fenoxaprop-(P)-ethyl + fenclorimfenoxaprop-(P)-ethyl + isoxadifen-ethyl fenoxaprop-(P)-ethyl +mefenpyr-diethyl pentoxazone bispyribac-sodium bromobutide benzofenapclomeprop dymron flufenacet oxaziclomefone propanil pyribenzoximpyriminobac-methyl quinoclamine azimsulfuron azimsulfuron + dymronazimsulfuron + bensulfuron-methyl bensulfuron-methylbensulfuron-methyl + dymron cinosulfuron cinosulfuron + dymroncyclosulfamuron cyclosulfamuron + dymron ethoxysulfuron ethoxysulfuron +dymron imazosulfuron imazosulfuron + dymron pyrazosulfuron-ethylpyrazosulfuron-ethyl + dymron fluazifop-P-butyl flucarbazone-sodiumflucarbazone-sodium + fenclorim flucarbazone-sodium + isoxadifen-ethylflucarbazone-sodium + mefenpyr-diethyl flufenacet flufenacet + 2,4-Dflufenacet + diflufenican flufenacet + metosulam flufenacet + propanilflufenacet + dichlormid flufenacet + furilazole flufenacet + R-29148flufenacet + fenclorim flufenacet + isoxadifen-ethyl flufenacet +mefenpyr-diethyl flumetsulam halosulfuron-methyl halosulfuron-methyl +cafenstrole + cyhalofop-butyl halosulfuron-methyl + cafenstrole + dymronhalosulfuron-methyl + cyhalofop-butyl + dymron haloxyfop-P-methylHOK-201 imazamox imazaquin imazethapyr imazosulfuron imazosulfuron +dymron imazosulfuron + anilofos imazosulfuron + benfuresateimazosulfuron + butachlor imazosulfuron + cafenstrole + dymronimazosulfuron + cyhalofop-butyl imazosulfuron + dimepiperateimazosulfuron + dimethametryn imazosulfuron + dimethametryn +pretilachlor imazosulfuron + esprocarb + dymron imazosulfuron +etobenzanid + Dymron imazosulfuron + mefenacet + Dymron imazosulfuron +oxaziclomefone imazosulfuron + pentoxazone + dymron imazosulfuron +pretilachlor + dymron imazosulfuron + pyributicarb + dymron indanofanisoxaflutole MCPA mefenacet mefenacet + molinate mefenacet +quinoclamine mefenacet + bromobutide + naproanilide mesosulfuronmesosulfuron + dymron mesosulfuron + anilofos mesosulfuron + benfuresatemesosulfuron + cafenstrole + dymron mesosulfuron + cyhalofop-butylmesosulfuron + dimepiperate mesosulfuron + esprocarb mesosulfuron +mefenacet mesosulfuron + mefenacet + dymron mesosulfuron +oxaziclomefone mesosulfuron + pretilachlor mesosulfuron + pyributicarbmesotrione metolachlor metolachlor + benoxacor S-metolachlorS-metolachlor + benoxacor metosulam metsulfuron-methyl metribuzinmolinate molinate + propanil molinate + simetryn naproanilidenicosulfuron OK-701 oxadiargyl oxadiargyl + propanil oxadiazonoxaziclomefone oxyfluorfen pendimethalin pentoxazone pentoxazone +cumyluron piperophos piperophos + 2,4-D pretilachlor pretilachlor +dimethametryn pretilachlor + dymron pretilachlor + dimethametryn +dymron pretilachlor + fenclorim profoxydim propanilpropoxycarbazone-sodium pyraclonil pyrazolate pyrazolate + butachlorpyrazolate + pretilachlor pyrazosulfuron-ethyl pyrazosulfuron-ethyl +dymron pyrazosulfuron-ethyl + indanofan pyrazosulfuron-ethyl +etobenzanid pyrazosulfuron-ethyl + esprocarb pyrazosulfuron-ethyl +esprocarb + dimethametryn pyrazosulfuron-ethyl + esprocarb +pretilachlor pyrazosulfuron-ethyl + mefenacet pyrazosulfuron-ethyl +molinate pyrazosulfuron-ethyl + pentoxazone pyrazosulfuron-ethyl +anilofos + dymron pyrazosulfuron-ethyl + benfuresate + dymronpyrazosulfuron-ethyl + butachlor + dymron pyrazosulfuron-ethyl +cafenstrole pyrazosulfuron-ethyl + cafenstrole + cyhalofop-butylpyrazosulfuron-ethyl + dimepiperate + dymron pyrazosulfuron-ethyl +dithiopyr + esprocarb pyrazosulfuron-ethyl + mefenacet + dymronpyrazosulfuron-ethyl + oxaziclomefone + dymron pyrazosulfuron-ethyl +pretilachlor pyrazosulfuron-ethyl + pretilachlor + quincloracpyrazosulfuron-ethyl + thenylchlor pyrazoxyfen pyribenzoxim pyributicarbpyributicarb + pretilachlor pyriftalid pyriminobac-methyl quincloracquinoclamine simazine simetryn sulcotrione terbuthylazine thenylchlorthifensulfuron-methyl tiocarbazil tritosulfuron

The active compound combinations according to the invention can be used,for example, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus andTaraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrosfis, Alopecurus, Apera and Phalaris.

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compound combinations according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

According to the invention, it is possible to treat all plants and partsof plants. By plants are understood here all plants and plantpopulations such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants can be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including the transgenic plants and including theplant varieties which can or cannot be protected by varietal propertyrights. Parts of plants are to be understood as meaning all above-groundand below-ground parts and organs of plants, such as shoot, leaf, flowerand root, examples which may be mentioned being leaves, needles, stems,trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubersand rhizomes. Parts of plants also include harvested material andvegetative and generative propagation material, for example seedlings,tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

The synergistic effect of the active compound combinations according tothe invention is particularly pronounced at certain concentrationratios. However, the ratios by weight of the active compounds in theactive compound combinations can be varied within relatively wideranges. In general, from 0.01 to 1000 parts by weight, preferably from0.1 to 100 parts by weight and particularly preferably from 0.1 to 10parts by weight of active compound of group 2 are present per part byweight of the active compound of the formula (I).

The advantageous effect of the crop plant compatibility of the activecompound combinations according to the invention is likewiseparticularly strongly pronounced at certain concentration ratios.However, the ratios by weight of the active compounds in the activecompound combinations can be varied within relatively wide ranges. Ingeneral, from 0.001 to 1000 parts by weight preferably from 0.01 to 100parts by weight and particularly preferably from 0.1 to 10 parts byweight of one of the compounds, mentioned above under (c), which improvecompatibility with crop plants (antidotes/safeners) are present per partby weight of active compound of the formula (I) or its mixtures withactive compounds of group 2.

The active compound combinations can be converted into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspo-emulsion concentrates, natural and synthetic substancesimpregnated with active compound, and very fine capsules in polymericsubstances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surface-active agents, thatis emulsifying agents and/or dispersing agents and/or foam-formingagents.

If the extender used is water it is also possible to use, for example,organic solvents as auxiliary solvents. Suitable liquid solvents are inthe main: aromatics, such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols, such as butanol orglycol as well as their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethyl sulphoxide, andalso water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as finely divided silica,alumina and silicates; suitable solid carriers for granules are: forexample crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, as well as synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks; suitableemulsifying and/or foam-forming agents are: for example nonionic andanionic emulsifiers, such as polyoxyethylene fatty acid esters,polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycolethers, alkylsulphonates, alkylsulphates, arylsulphonates as well asprotein hydrolysates; suitable dispersing agents are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general comprise between 0.1 and 95 percent byweight, preferably between 0.5 and 90%, of active compounds.

In general, the active compound combinations according to the inventionare applied in the form of ready mixes. However, the active compoundswhich the active compound combinations comprise can also be formulatedindividually and mixed upon use, i.e. applied in the form of tank mixes.

The novel active compound combinations can be used as such or in theform of their formulations, and furthermore also as mixtures with otherknown herbicides, ready mixes or tank mixes again being possible. Theymay also be mixed with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, growthsubstances, plant nutrients and agents which improve soil structure. Forparticular application purposes, in particular when appliedpost-emergence, it may furthermore be advantageous to incorporate, inthe formulations, mineral or vegetable oils which are tolerated byplants (for example the commercial product “Oleo DuPont 11E”) orammonium salts such as, for example, ammonium sulphate or ammoniumthiocyanate, as further additives.

The novel active compound combinations can be used as such, in the formof their formulations or in the use forms prepared therefrom by furtherdilution, such as ready-to-use solutions, suspensions, emulsions,powders, pastes and granules. They are used in the customary manner, forexample by watering, spraying, atomising, dusting or scattering.

The active compound combinations according to the invention can beapplied before and after the plants have emerged, that is to saypre-emergence and post-emergence. They can also be incorporated into thesoil before sowing.

A synergistic effect in herbicides is always present when the herbicidalactivity of the active compound combination exceeds the activity of theactive compounds when applied individually.

The expected activity for a given combination of two herbicides can becalculated as follows (cf. COLBY, S. R.: “Calculating synergistic andantagonistic responses of herbicide combinations”, Weeds 15, pages20-22, 1967):

-   If X=% damage by herbicide A (active compound of the formula I) at    an application rate of p kg/ha-   and Y=% damage by herbicide B (active compound of the formula II) at    an application rate of q kg/ha-   and E=the expected damage of the herbicides A and B at application    rates of p and q kg/ha,-   then E=X+Y−(X*Y/100).

If the actual damage exceeds the calculated value, then the activity ofthe combination is superadditive, i.e. a synergistic effect exists.

USE EXAMPLES Example A Test in Sown Rice (Brazil)

To prepare a spray preparation, the active compound preparations aremixed with water. The concentration is adjusted so that the applicationrate corresponds to 200 l of water/ha.

Rice seeds are sown in test plots (2 m×5 m) in rice paddies. 10 daysafter sowing (when the rice has reached the 1-2-leaf stage), the spraypreparation is applied to the test areas (using a hand-operatedsprayer). 1 month after the treatment, the soil is flooded to a waterdepth of 5 cm; the standing water levels are kept constant.

3 weeks after the active compound application, the degree of damage tothe rice plants and the herbicidal effect on the emerged weeds of thespecies Aeschynomene rudis is scored visually in percent in comparisonto an untreated control.

The figures denote:

-   -   0%=no action/damage (like untreated control)    -   100%=total destruction.

The results are shown in the table below. TABLE A-1 Test plants Damageor action in % Active Application rate Aeschynomene Paddy rice compoundor g/ha rudis (Oryza sp.) combination (active compound) found calc.found calc. (A) 400 30 0 -known- (B)  40 90 0 -known- (A) + (B) 400 + 4095 (93) 0 -according to the invention-calc. = calculatedA fentrazamide 250 EC 400 g a.i./haB bispyribac-sodium 400 SC 40 g a.i./haA + B fentrazamide 250 EC + Bispyribac-sodium 400 SC 400 + 40 g a.i./haOutdoor test in sown rice (Brazil 1999)Spray application during the 1-2-leaf stage of the rice

Example B Test in Sown Rice (Brazil)

To prepare a spray preparation, the active compound preparations aremixed with water. The concentration is adjusted so that the applicationrate corresponds to 200 l of water/ha.

Rice seeds are sown in test plots (2 m×5 m) in rice paddies. 29 daysafter sowing (during the BBCH 23 development stage of the rice; begin ofstocking), the spray preparation is applied to the test areas (using ahand-operated sprayer). A few days after the treatment, the soil isflooded to a water depth of 5 cm; the standing water levels are keptconstant.

2 weeks after the active compound application, the degree of damage tothe rice plants and the herbicidal effect on the emerged weedsEchinochloa crus-galli and Brachiaria plantaginea is scored visually inpercent in comparison to an untreated control.

The figures denote:

-   -   0%=no action/damage (like untreated control)    -   100%=total destruction.

The results are shown in the table below. TABLE B-1 Test plants ActiveApplication Damage or action in % compound rate g/ha EchinochloaBrachiaria Paddy rice or combi- (active crus-galli plantaginea (Oryzasp.) nation compound) found calc. found calc. found calc. (A) 300 35 100 -known- (B) 75 70 85 8 -known- (A) + (B) 300 + 75 90 (80.5) 93 (86.5)10 -according to the invention-calc. = calculatedA fentrazamide 250 EC 300 g a.i./haB profoxydim 200 EC 75 g a.i./haA + B fentrazamide 250 EC + profoxydim 200 EC 300 + 75 g a.i./haOutdoor test in sown rice (Brazil 1999)Spray application during the BBCH 23 stage of the rice (begin ofstocking)

Example C Test in Sown Rice (Brazil)

To prepare a spray preparation, the active compound preparations aremixed with water. The concentration is adjusted so that the applicationrate corresponds to 200 l of water/ha.

Rice seeds are sown in test plots (2 m×5 m) in rice paddies. 29 daysafter sowing (during the BBCH 23 development stage of the rice; begin ofstocking), the spray preparation is applied to the test areas (using ahand-operated sprayer). A few days after the treatment, the soil isflooded to a water depth of 5 cm; the standing water levels are keptconstant.

2 weeks after the active compound application, the degree of damage tothe rice plants and the herbicidal effect on the emerged weedsEchinochloa crus-galli and Brachiaria plantaginea is scored visually inpercent in comparison to an untreated control.

The figures denote:

-   -   0%=no action/damage (like untreated control)    -   100%=total destruction.

The results are shown in the table below. TABLE C-1 Test plants ActiveApplication Damage or action in % compound rate g/ha EchinochloaBrachiaria Paddy rice or combi- (active crus-galli plantaginea (Oryzasp.) nation compound) found calc. found calc. found calc. (A) 300 35 100 -known- (B) 75 70 85 8 -known- (A) + (B) 150 + 75 85 (80.5) 90 (86.5)10 -according to the invention-calc. = calculatedA fentrazamide 250 EC 300 g a.i./haB profoxydim 200 EC 75 g a.i./haA + B fentrazamide 250 EC + profoxydim 200 EC 150 + 75 g a.i./haOutdoor test in sown rice (Brazil 1999)Spray application during the BBCH 23 stage of the rice (begin ofstocking)

Example D Test in Sown Rice (Brazil)

To prepare a spray preparation, the active compound preparations aremixed with water. The concentration is adjusted so that the applicationrate corresponds to 200 l of water/ha.

Rice seeds are sown in test plots (2 m×5 m) in rice paddies. 29 daysafter sowing (during the BBCH 23 development stage of the rice; begin ofstocking), the spray preparation is applied to the test areas (using ahand-operated sprayer). A few days after the treatment, the soil isflooded to a water depth of 5 cm; the standing water levels are keptconstant.

2 weeks after the active compound application, the degree of damage tothe rice plants and the herbicidal effect on the emerged weedsEchinochloa crus-galli and Brachiaria plantaginea is scored visually inpercent in comparison to an untreated control.

The figures denote:

-   -   0%=no action/damage (like untreated control)    -   100%=total destruction.

The results are shown in the table below. TABLE D-1 Test plantsApplication Damage or action in % Active rate g/ha EchinochloaBrachiaria Paddy rice compound or (active crus-galli plantaginea (Oryzasp.) combination compound) found calc. found calc. found calc. (A) 30035 10 0 -known- (B) 100 75 80 10 -known- (A) + (B) 300 + 100 85 (83) 93(82) 10 -according to the invention-calc. = calculatedA fentrazamide 250 EC 300 g a.i./haB profoxydim 200 EC 100 g a.i./haA + B fentrazamide 250 EC + profoxydim 200 EC 300 + 100 g a.i./haOutdoor test in sown rice (Brazil 1999)Spray application during the BBCH 23 stage of the rice (begin ofstocking)

Example E Test in Sown Rice (Brazil)

To prepare a spray preparation, the active compound preparations aremixed with water. The concentration is adjusted so that the applicationrate corresponds to 200 l of water/ha.

Rice seeds are sown in test plots (2 m×5 m) in rice paddies. 29 daysafter sowing (during the BBCH 23 development stage of the rice; begin ofstocking), the spray preparation is applied to the test areas (using ahand-operated sprayer). A few days after the treatment, the soil isflooded to a water depth of 5 cm; the standing water levels are keptconstant.

2 weeks after the active compound application, the degree of damage tothe rice plants and the herbicidal effect on the emerged weedsEchinochloa crus-galli and Brachiaria plantaginea is scored visually inpercent in comparison to an untreated control.

The figures denote:

-   -   0%=no action/damage (like untreated control)    -   100%=total destruction.

The results are shown in the table below. TABLE E-1 Test plantsApplication Damage or action in % Active rate g/ha EchinochloaBrachiaria Paddy rice compound or (active crus-galli plantaginea (Oryzasp.) combination compound) found calc. found calc. found calc. (A) 30035 10 0 -known- (B) 100 75 80 10 -known- (A) + (B) 150 + 100 85 (83) 90(82) 13 -according to the invention-calc. = calculatedA fentrazamide 250 EC 300 g a.i./haB profoxydim 200 EC 100 g a.i./haA + B fentrazamide 250 EC + profoxydim 200 EC 150 + 100 g a.i./haOutdoor test in sown rice (Brazil 1999)Spray application during the BBCH 23 stage of the rice (begin ofstocking)

Example F Test in Sown Rice (Brazil)

To prepare a spray preparation, the active compound preparations aremixed with water. The concentration is adjusted so that the applicationrate corresponds to 200 l of water/ha.

Rice seeds are sown in test plots (2 m×5 m) in rice paddies. 18 daysafter sowing (during the BBCH 12 development stage of the rice;corresponds to the 2-leaf-stage), the spray preparation is applied tothe test areas (using a hand-operated sprayer).

3 weeks after the active compound application, the degree of damage tothe rice plants and the herbicidal effect on the emerged weedsAcanthospermum hispidum, Commelina benghalensis, Digitaria sanguinalisand Eleusine indica is scored visually in percent in comparison to anuntreated control.

The figures denote:

-   -   0%=no action/damage (like untreated control)    -   100%=total destruction.

The results are shown in the table below. TABLE F-1 Test plants Damageor action in % Application Acantho- Commelina Mountain Active rate g/haspermum Bengha- Digitaria Eleusine rice compound or (active hispidumlensis Sanguina-lis indica (Oryza sp.) combination compound) found calc.found calc. found calc. found calc. found calc. (A) 300 50 50 50 50 0-known- (B) 100 40 40 50 50 0 -known- (A) + (B) 150 + 100 80 (70) 80(70) 80 (75) 80 (75) 0 -according to the invention-calc. = calculatedA fentrazamide 250 EC 300 g a.i./haB profoxydim 200 EC 100 g a.i./haA + B fentrazamide 250 EC + profoxydim 200 EC 150 + 100 g a.i./haOutdoor test in sown rice (Brazil 1999)Spray application during the BBCH 12 stage of the rice (2-leaf-stage)

Example G Test in Sown Rice (Philippines)

To prepare a spray preparation, the active compound preparations aremixed with water. The concentration is adjusted so that the applicationrate corresponds to 200 l of water/ha.

Rice seeds are sown in test plots (2.5 m×2.5 m) in rice paddies. 11 daysafter sowing (4-leaf-stage of the rice), the spray preparation isapplied to the test areas (using a hand-operated sprayer). 1 day afterthe treatment, the soil is flooded to a water depth of 5 cm; thestanding water levels are kept constant.

8 weeks after the active compound application, the degree of damage tothe rice plants and the herbicidal effect on the emerged weeds of thespecies Echinochloa crus-galli is scored visually in percent incomparison to an untreated control.

The figures denote:

-   -   0%=no action/damage (like untreated control)    -   100%=total destruction.

The results are shown in the table below. TABLE G-1 Test plantsApplication Damage or action in % Active rate g/ha Echinochloa Paddyrice compound or (active crus-galli (Oryza sp.) combination compound)found calc. found calc. (A) 135 78 0 -known- (B) 75 50 0 -known- (A) +(B) 135 + 75 93 (89) 2 -according to the invention-calc. = calculatedA fentrazamide 50 WP 135 g a.i./haB profoxydim 200 EC 75 g a.i./haA + B fentrazamide 50 WP + profoxydim 200 EC 135 + 75 g a.i./haOutdoor test in sown rice (Philippines 1999)Spray application 11 days after sowing

Example H Test in Sown Rice (Thailand)

To prepare a spray preparation, the active compound preparations aremixed with water. The concentration is adjusted so that the applicationrate corresponds to 200 l of water/ha.

Rice seeds are sown in test plots (2.5 m×2.5 m) in rice paddies. 7 daysafter sowing (2-leaf-stage of the rice), the spray preparation isapplied to the test areas (using a hand-operated sprayer). 2 days afterthe treatment, the soil is flooded to a water depth of 5 cm; thestanding water levels are kept constant.

8 weeks after the active compound application, the degree of damage tothe rice plants and the herbicidal effect on the emerged weedsEchinochloa crus-galli and Leptochloa chinensis is scored visually inpercent in comparison to an untreated control.

The figures denote:

-   -   0%=no action/damage (like untreated control)    -   100%=total destruction.

The results are shown in the table below. TABLE H-1 Test plantsApplication Damage or action in % Active rate g/ha EchinochloaLeptochloa Paddy rice compound or (active crus-galli chinensis (Oryzasp.) combination compound) found calc. found calc. found calc. (A) 13547 38 3 -known- (B) 50 60 63 0 -known- (A) + (B) 135 + 50 85 (79) 85(77) 5 -according to- the invention-calc. = calculatedA fentrazamide 50 WP 135 g a.i./haB profoxydim 200 EC 50 g a.i./haA + B fentrazamide 50 WP + profoxydim 200 EC 135 + 50 g a.i./haOutdoor test in sown rice (Thailand 1999)Spray application 7 days after sowing

Example I Test in Sown Rice (Thailand)

To prepare a spray preparation, the active compound preparations aremixed with water. The concentration is adjusted so that the applicationrate corresponds to 200 l of water/ha.

Rice seeds are sown in test plots (2.5 m×2.5 m) in rice paddies. 7 daysafter sowing (2-leaf-stage of the rice), the spray preparation isapplied to the test areas (using a hand-operated sprayer). 2 days afterthe treatment, the soil is flooded to a water depth of 5 cm; thestanding water levels are kept constant.

3 weeks after the active compound application, the degree of damage tothe rice plants and the herbicidal effect on the emerged weedsEchinochloa crus-galli is scored visually in percent in comparison to anuntreated control.

The figures denote:

-   -   0%=no action/damage (like untreated control)    -   100%=total destruction.

The results are shown in the table below. TABLE I-1 Test plants Damageor action in % Active Application rate Echinochloa Paddy rice compoundor g/ha crus-galli (Oryza sp.) combination (active compound) found calc.found calc. (A) 135 58 2 -known- (B)  50 63 0 -known- (A) + (B) 135 + 5092 (84) 6 -according to the invention-calc. = calculatedA fentrazamide 50 WP 135 g a.i./haB profoxydim 200 EC 50 g a.i./haA + B fentrazamide 50 WP + profoxydim 200 EC 135 + 50 g a.i./haOutdoor test in sown rice (Thailand 1999)Spray application 7 days after sowing

1-9. (canceled)
 10. A composition comprising an effective amount of anactive compound combination comprising (a) the compound4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide(fentrazamide) of formula (I)

and (b) one or more compounds selected from a second group of herbicidesconsisting of 2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoic acid andits salts, diphenylmethanoneO-[2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]-benzoyl]oxime(pyribenzoxim), 7-[(4,6-dimethoxy-2-pyrimidinyl)thio]-3-methyl-1(3H)-isobenzofuranone (pyriftalid),1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]pyridin-2-yl)-5-(methyl-2-propynylamino)-1H-pyrazole-4-carbonitrile(pyraclonil),N-(2,6-dichloro-3-methylphenyl)-5,7-dimethoxy-[1,2,4]-triazolo-[1,5-a]pyrimidine-2-sulphonamide(metosulam),2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulphonyl]benzoicacid (metsulphuron), methyl3-chloro-5-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]-carbonyl]amino]sulphonyl]-1-methyl-1H-pyrazole-4-carboxylate(halosulphuron),α-2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-4-fluorobenzenepropanoicacid esters,4-[2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulphonylbenzoyl]-5-hydroxy-1-methyl-1H-pyrazole,1-methylethyl5-[4-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-2-chloro-4-fluorobenzoate(fluazolate),2-[1-[[2-(4-chlorophenoxy)propoxy]amino]butyl]-5-(tetrahydro-2H-thiopyran-3-yl)-1,3-cyclohexanedione(clefoxydim),N-(2,4-difluorophenyl-1,5-dihydro-N-1-propyl-5-oxo-1-[(tetrahydro-2H-pyran-2-yl)methyl]-4H-1,2,4-triazole-4-carboxamide(HOK-201),4-(7-chloro-2,4-dimethyl-5-benzofuranyl)-2,4-dihydro-2-methyl-5-trifluoromethyl-3H-1,2,4-triazol-3-thione(OK-701),[2-chloro-3-(4,5-dihydro-3-isoxazolyl)-4-methylsulphonylphenyl]-(5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone,[3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-methylsulphonylphenyl]-(5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone,[3-[2-chloro-3-[(2,6-dioxocyclohexyl)carbonyl]-6-ethylsulphonylphenyl]-5-isoxazolyl]acetonitrile,2-[2-chloro-4-methylsulphonyl-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-1,3-cyclohexanedione,and2-[[5,8-dimethyl-1,1-dioxido-4-(2-pyrimidinyloxy)-3,4-dihydro-2H-thiochromen-6-yl]-carbonyl]-1,3-cyclohexanedione;and, optionally, (c) one or more compounds that improves crop plantcompatibility selected from the group consisting of the compoundsα-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil),α-(cyanomethoximino)phenylacetonitrile (cyometrinil),4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime(fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim),4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),1-methylhexyl 5-chloroquinoxaline-8-oxyacetate (cloquintocet),2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide(DKA-24), 1,8-naphthalic anhydride, ethyl1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate(fenchlorazole ethyl), phenylmethyl2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole,MON-13900), 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]-decane (AD-67),2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide(PPG-1292), 2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid),N-(4-methylphenyl)-N′-(1-methyl-1-phenylethyl)urea (dymron),1-dichloroacetylhexahydro-3,3,8a-trimethyl-pyrrolo[1,2-a]pyrimidin-6(2H)one(BAS-145138),N-(2-methoxybenzoyl)-4-(methylaminocarbonylamino)benzenesulphonamide,ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate(isoxadifen-ethyl), (4-chloro-2-methylphenoxy)acetic acid (MCPA),2-(4-chloro-2-methylphenoxy)propionic acid (mecoprop),diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazol-3,5-dicarboxylate(mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and itsderivatives, 4-(2-chlorobenzoylaminosulphonyl)-N-propyl-benzamide,N-(phenylsulphamoyl)benzamide derivatives of formula (II)

in which R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,(C₂-C₆)-alkenyl, (C₅-C₆)-cycloalkenyl, phenyl, or 3- to 6-memberedheterocyclyl having up to 3 hetero atoms selected from the groupconsisting of nitrogen, oxygen, and sulphur, where the radicals R¹ otherthan hydrogen are optionally substituted by one or more identical ordifferent substituents selected from the group consisting of halogen,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₂)-alkylsulfinyl,(C₁-C₂)-alkylsulfonyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxycarbonyl,(C₁-C₄)-alkylcarbonyl, and phenyl and the cyclic radicals are optionallyalso substituted by (C₁-C₄)-alkyl or (C₁-C₄)-haloalkyl; R² representshydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, where theradicals R² other than hydrogen are optionally substituted by one ormore identical or different substituents selected from the groupconsisting of halogen, hydroxyl, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, and(C₁-C₄)-alkylthio; R³ represents halogen, (C₁-C₄)-haloalkyl,(C₁-C₄)-haloalkoxy, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-alkylsulphonyl, (C₁-C₄)-alkoxycarbonyl, or(C₁-C₄)-alkylcarbonyl; R⁴ represents hydrogen or methyl; R⁵ representshalogen, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,(C₃-C₆)-cycloalkyl, phenyl, (C₁-C₄)-alkoxy, cyano, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-alkoxycarbonyl,or (C₁-C₄)-alkylcarbonyl; n represents 0, 1, or 2, and m represents 1 or2, or salts thereof, and2-methoxy-N-[4-(methoxybenzoylsulphamoyl)phenyl]acetamide and otherN-acylsulphonamide derivatives of formula (III)

in which R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,furanyl, or thienyl, where each of the radicals R¹ other than hydrogenis unsubstituted or substituted by one or more substituents selectedfrom the group consisting of halogen, (C₁-C₄)-alkoxy,halo-(C₁-C₆)-alkoxy, and (C₁-C₄)-alkylthio and the cyclic radicals areoptionally also substituted by (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl; R²represents hydrogen or methyl; R³ represents halogen,halo-(C₁-C₄)-alkyl, halo-(C₁-C₄)-alkoxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-alkylsulphonyl, (C₁-C₄)-alkoxycarbonyl, or(C₁-C₄)-alkylcarbonyl; R⁴ represents hydrogen or methyl; R⁵ representshalogen, (C₁-C₄)-alkyl, halo-(C₁-C₄)-alkyl, halo-(C₁-C₄)-alkoxy,(C₃-C₆)-cycloalkyl, phenyl, (C₁-C₄)-alkoxy, cyano, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-alkoxycarbonyl,or (C₁-C₄)-alkylcarbonyl; n represents 0, 1, or 2, and m represents 1 or2, or alkali metal salts thereof.
 11. A composition according to claim10 wherein component (b) is bispyribac-sodium and/or pyribenzoxim.
 12. Acomposition according to claim 10 wherein component (b) isbispyribac-sodium.
 13. A composition according to claim 10 whereincomponent (b) is pyribenzoxim.
 14. A composition according to claim 10wherein from 0.01 to 1,000 parts by weight of the active compound ofcomponent (b) are present per part by weight of the active compound offormula (I).
 15. A composition according to claim 10 wherein from 0.001to 1,000 parts by weight of component (c) are present per part by weightof the active compound of formula (I) or mixtures of the active compoundof formula (I) with active compounds of component (b).
 16. A method forcontrolling unwanted vegetation comprising allowing an effective amountof a composition according to claim 10 to act on plants and/or theirhabitat.
 17. A process for preparing a composition according to claim 10comprising mixing active compounds of components (a) and (b) and,optionally, component (c) with one or more extenders and/or surfactants.